Cyclopropylboronic acid → Tert-butyl 4-(adamantan-1-ylmethoxy)-5-cyclobutyl-2-fluorobenzoate

HRID 1849840Notes

Reaction equation

HRID 1849840 reaction equation
Cl[C:2]1[C:3]([O:16][CH2:17][C:18]2([C:24]#N)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C12(CO[C:38]3[C:50](Cl)=[CH:49][C:41](C(OC(C)(C)C)=O)=C(F)C=3)CC3CC(CC(C3)C1)C2.[CH:53]1(B(O)O)[CH2:55][CH2:54]1.C1(B(O)O)CCC1.F[B-](F)(F)F.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1>>[C:18]12([CH2:17][O:16][C:3]3[C:2]([CH:41]4[CH2:49][CH2:50][CH2:38]4)=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([F:15])[CH:4]=3)[CH2:23][CH:22]3[CH2:54][CH:53]([CH2:55][CH:20]([CH2:21]3)[CH2:19]1)[CH2:24]2

Participants

7

Reactant 6

HCID 2760897Cyclopropylboronic acidHCID 16217845Cyclobutylboronic acidHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 20066521Tri(cyclohexyl)phosphine tetrafluoroborateHCID 86702858Tert-butyl 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoateHCID 86703716Tert-butyl 5-chloro-4-((1-cyanocyclohexyl)methoxy)-2-fluorobenzoate

Product 1

HCID 86703727Tert-butyl 4-(adamantan-1-ylmethoxy)-5-cyclobutyl-2-fluorobenzoate

Procedure

Following the procedure as described in Example 373 Step 1 and making non-critical variations to replace tert-butyl 5-chloro-4-((1-cyanocyclohexyl)-methoxy)-2-fluorobenzoate with tert-butyl 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoate, to replace cyclopropylboronic acid with cyclobutylboronic acid, and to replace tricyclohexylphosphine tetrafluoroborate with 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (RuPhos), the title compound was obtained as a colorless syrup containing ˜25% tert-butyl 4-(adamantan-1-ylmethoxy)-2-fluorobenzoate (1.01 g, 97%): MS (ES+) m/z 359.1 (M−55).

Sources & evidence

ORD record
ord-8344d59c44a646839044e54d9c1d4d75
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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